My understanding was that the "personal item" had to fit under your seat (No rollerboards).

If I recall, the common description goes something like "You are limited to two items, One larger item such as a rollerboard and a smaller item such as a purse or backpack" I believe this started due to female passengers bringing two items PLUS their purse (some of which are pretty good size). - please no offense meant to anyone.

Sorry, but I think you got lucky 4x and met reality on the 5th leg.

I don't blame the GA for following the rules - I don't think you should either.